We caught up with the brilliant and insightful Courtney Benson a few weeks ago and have shared our conversation below.

Alright, Courtney thanks for taking the time to share your stories and insights with us today. One deeply underappreciated facet of entrepreneurship is the kind of crazy stuff we have to deal with as business owners. Sometimes it’s crazy positive sometimes it’s crazy negative, but crazy experiences unite entrepreneurs regardless of industry. Can you share a crazy story with our readers?

Craziest (but best) thing that ever happened to me in business? Here’s the truth.

In 2009, I went from flying high to flat broke. I had been a successful executive in the cosmetic industry, a celebrity make up artist. I managed eight states, ran trainings, and worked with brands like MAC, Sephora, and Nordstrom. I loved that life. It felt secure.

Then the economy crashed.

Trying to pivot, my husband and I opened two dry cleaning business in Frisco. We thought it would save us, but it barely kept the lights on. It wasn’t making money, and it drained what little we had left. We were in survival mode.

So I started cleaning houses on the side just to afford groceries, my husband got a second job and helped me clean too. I’d go into people’s homes, scrub floors and clean toilets. Some of the houses weren’t even as nice as the one we had just lost.

We had two babies under five. A $60 a week grocery budget. No savings. Our car had been repossessed. My marriage was hanging by a thread. I had gained a lot of weight and felt invisible. It was one of the lowest points of my life.

I was sitting in the back of the dry cleaning store one afternoon, working on some interior design boards for a client, just another side hustle I had picked up, when a Groupon ad popped up on my screen.

“Become a Real Estate Agent… $199.” We had $237 in our bank account.

I clicked it and bought it without thinking, then instantly panicked. I started crying. I called my husband, even though we weren’t in a good place. I told him what I had spent all of our money and Groupon didn’t allow me to return it (I tried!). He said, “You’re going to be great.”

It took me a full year to get through the coursework. I was cleaning houses and working at the dry cleaner during the day, raising kids at night, and studying in the pockets of time in between. I didn’t know where I was headed or how to do it, but I just kept going.

This year, I was named in the top 1 percent of realtors in the country by the Wall Street Journal for the 3rd year in a row. I’ve lost 130 pounds. I’ve built a business and a brand by showing up as myself… no fluff, just real talk.

That $199 Groupon changed my life.

It was the scariest thing I ever did. And it turned out to be the best thing I ever did. My husband and I climbed out together.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I got into real estate out of complete naivety, sheer hope and a lot of grit. My business really started to grow when I stopped people pleasing and started trusting myself, when I got clear on what I bring to the table and what I absolutely will not do for a paycheck. My “why” is freedom. I want a life that feels good, not just one that looks good on social media or a spreadsheet.

Today, I help buyers, sellers and developers from Dallas to North Dallas, Tx build real estate portfolios, find dream homes, or just for right now homes depending on what life looks like for them. It’s an honor. I’m known for being direct, resourceful, and fully in it with my clients from start to finish. I’m a fierce negotiator, a clear communicator, and a true partner in the process. My clients know I’ve got their back.

I love marketing and strategic negotiation, I show up big online, but behind the social media is someone who knows her stuff, I am good at the craft of real estate and I am proud of that.

Outside of my client business, I’m also the founder of The Happy Agent, a podcast, FB Group (The Happy Agent Collective), a coaching platform, and a community for real estate pros who are done with the hustle-all-day mindset. I teach agents how to attract clients and build businesses that actually feel good. It’s about confidence, clarity, and showing up as yourself without burning out.

At the heart of it all, my brand is rooted in authenticity. What you see is what you get, whether I’m helping you buy your dream home, sell your current one, or build a business that finally feels like yours. I’ve built a career I love by showing up fully as myself with people I love inspiring me and cheering me on all the way. This isn’t just because of me, there have been so many that pulled me up along the way, always find your people, it will make or break you.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

A big lesson I had to unlearn is that things have to be hard first in order to become successful, or worth it. I used to believe that struggle was the only path to success, and that if something came easily or felt joyful, it wasn’t valuable. I thought I had to grind, hustle, and prove myself nonstop for the results to “count.”

But over time, I realized that belief was just holding me back. It is a self sabotaging belief.

I had to learn how to let good things be good. I had to learn how to celebrate wins, big and small, without bracing for something bad to follow. It’s not arrogant to be proud of yourself. It’s not selfish to enjoy your life. And it doesn’t take anything away from anyone else when you succeed. In fact, sharing your wins can show others what’s possible and help them believe in their own path too.

Now, I see success as something collaborative and expansive. The more I let myself enjoy it, the more I seem to attract. And that shift has changed everything for me, not just in business, but in how I show up for life.

Any insights you can share with us about how you built up your social media presence?

I built my audience on social media by staying consistent with my message. My message is real estate, and I show that through my personality, by the way I talk, where I film, what I’m wearing, and how I handle situations. People don’t just see the houses. They see me. They hear my voice, they hear my opinions, and they learn how I show up for my clients through storytelling, humor, and straight talk. I share real estate in a way that only I can, and I stay true to that no matter what’s trending.

My advice? Figure out who you are, what you want to say, and how you want to say it. Then practice that every single day. You don’t have to go viral to grow. You just have to be consistent. Whatever you do daily will lead to a result — so pick something worth repeating. Be clear with your story and stick to it. Your people will find you.

Contact Info:

• Website: https://www.heyitscourtneybenson.com/
• Instagram: https://www.instagram.com/courtneybensondotcom/
• Youtube: https://www.youtube.com/channel/UCFUfXTeGfzKa5Ggo9zo3Tzg
• Other: TikTok: https://www.tiktok.com/@heyitscourtneybenson

Image Credits

None